U.S. Pat. No. 3,282,875 shows the following decarboxylation reaction ##STR2## where R.sub.f is F or a perfluoroalkyl radical having from 1-10 carbon atoms;
y is F or trifluoromethyl radical; PA1 n is an integer of 1-3, inclusive; PA1 M is F, hydroxyl radical, amino radical or OMe; and PA1 Me is an alkali metal or a quaternary nitrogen radical. PA1 b=0 or an integer greater than 0 PA1 n=1 or an integer greater than 1; PA1 R.sub.f and R.sub.f ' are independently selected from the group consisting of F, Cl, perfluoroalkyl or fluorochloroalkyl; PA1 X=F, Cl, Br or mixtures thereof n&gt;1 PA1 X'=Cl or Br; PA1 D is an acid group or an acid derivative easily converted to an acid group; PA1 Z=F, Cl, Br, OH, NRR' or OA; PA1 R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atoms, and aryl; and PA1 A=alkali metal, quaternary nitrogen, or R. PA1 b is 0 or an integer greater than 0; PA1 n is one or an integer greater than one; PA1 R.sub.f ' and R.sub.f =are independently selected from the group consisting of F, Cl, perfluoroalkyl and fluorochloroalkyl; PA1 X=F, Cl, Br or mixtures thereof when n&gt;1; PA1 X'=Cl or Br; PA1 D is an acid group or an acid derivative easily convertible to an acid group. PA1 Z=F, Cl, Br, OH, NRR' or OA; PA1 R and R'=are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atoms, and aryl; and PA1 A=alkali metal, quaternary nitrogen, or R. PA1 X=Cl, Br or mixtures thereof when n&gt;1; PA1 D=an acid group or an acid derivative easily convertible to an acid group; PA1 R.sub.f and R.sub.f ' are independently selected from the group consisting of F, Cl, and perfluoroalkyl radical and a chlorofluoroalkyl radical; PA1 a=0 or an integer greater than 0; PA1 b=0 or an integer greater than 0.
Yields in the decarboxylation reaction of about 80% were obtained at high temperatures (about 300.degree. C.) while yields of 20-30% were obtained at lower temperatures (about 200.degree. C.). Also taught is the homo and copolymerization of the vinyl ether monomers to form useful polymers.
British Pat. No. 1,518,387 teaches the following reactions ##STR3##
Copolymers of the vinylether monomers with tetrafluoroethylene were shown to be useful as membranes in chlor-alkali electrolytic cells.
Fearn, et al. Journal of Polymer Science, Volume 4, pp. 131-140, "Polymers and Terpolymers of Perfluoro-1,4-pentadiene" discloses that in the pyrolysis of sodium salts of carboxylic acids which contain fluorine and chlorine in the .beta. position, sodium chloride is preferentially, but not exclusively eliminated. For example ##STR4##
German Pat. No. 1,238,458 teaches that useful polymers are made from compounds of the general structure ##STR5## where n=1-8, p=0-5 and m=0-5. Crosslinked halogenated olefin copolymers are produced making use of the iodine group as a reactive site.
R. D. Chambers, in his book, Fluorine in Organic Chemistry, published by John Wiley & Sons, 1973, pages 211-212, teaches that carboxylic acid derivatives may be converted to olefins. The conversion is taught to involve the loss of carbon dioxide and formation of an intermediate carbanion. The intermediate then loses NaF to form the resulting olefin.
Numerous patents and publications have taught the use of acid functional fluorocarbon polymers in chlor-alkali electrolytic cells (British Pat. Nos. 1,497,748; 1,497,749; 1,518,387 and U.S. Pat. Nos. 3,784,399; 3,969,285; 4,025,405).